Triethylamine → HCID 70381148, compound

HRID 1247994Notes

Reaction equation

HRID 1247994 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[C@@H:16]([OH:17])[C:15](=[O:18])[N:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]=3[S:11]2)=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.[Cl:35][C:36]1[CH:44]=[C:43]([N+:45]([O-:47])=[O:46])[CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[C@@H:16]([O:17][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][C:43]([N+:45]([O-:47])=[O:46])=[CH:44][C:36]=3[Cl:35])[C:15](=[O:18])[N:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]=3[S:11]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 70381258HCID 70381258, compound

Product 1

HCID 70381148HCID 70381148, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.04 g of (+)-cis-2-(4-ethoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are dissolved in 20 ml of anhydrous benzene, and 1 ml of triethylamine is added thereto. A solution of 0.62 g of 2-chloro-4-nitrobenzoyl chloride in 2 ml of anhydrous benzene is added to the mixture under stirring, and said mixture is stirred at room temperature for 0.5 hour. After the reaction, the mixture is washed with water, dried and condensed to dryness. The residue is recrystallized from ethanol, whereby 0.94 g of (+)-cis-2-(4-ethoxyphenyl)-3-(2-chloro-4-nitrobenzoyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is obtained as pale yellow needles. Yield: 61%.

Workup

  1. stirringis stirred at room temperature for 0.5 hour
  2. customAfter the reaction
  3. washthe mixture is washed with water
  4. customdried
  5. customcondensed to dryness
  6. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-2bd4fba5e225485b87ce9c87098fbcfc
Source dataset
uspto-grants-1985_06
Patent number
US04521430

Reaction notes

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